Oxalyl chloride → Pyrimidine-5-carbonyl chloride

Participants

Reaction Steps

The titled compound was prepared according to the procedure of Method D using 3,4-difluoro-N′-hydroxybenzimidamide (Tyger) and pyrimidine-5-carbonyl chloride. The pyrimidine-5-carbonyl chloride was prepared by the reaction of pyrimidine-5-carboxylic acid (Maybridge, 138 mg, 1.0 mmol) with oxalyl chloride (Aldrich, 2 M, in CH2Cl2, 1.0 mL, 2.0 mmol) and a drop of dimethylformamide at room temperature over 1 hour with subsequent removal of volatiles under reduced pressure. 1H NMR (300 MHz, DMSO-d6) δ 7.72 (dt, J=10.5, 8.5 Hz, 1H), 7.94-8.05 (m, 1H), 8.11 (ddd, J=10.9, 7.7, 2.0 Hz, 1H), 8.12 (none, 1H), 9.51 (s, 1H), 9.54 (s, 2H) ppm; MS (DCI/NH3) m/z 261 (M+H)+.

Provenance & Evidence